Ethyl orthoformate → 6-bromo-3-methyl-4(3H)-Pteridinone

HRID 2242903Notes

Reaction equation

HRID 2242903 reaction equation
[CH:1](OCC)(OCC)OCC.[CH3:11][NH:12][C:13]([C:15]1[C:20]([NH2:21])=[N:19][CH:18]=[C:17]([Br:22])[N:16]=1)=[O:14]>C(OC(=O)C)(=O)C>[Br:22][C:17]1[N:16]=[C:15]2[C:20](=[N:19][CH:18]=1)[N:21]=[CH:11][N:12]([CH3:1])[C:13]2=[O:14]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 151481213-Amino-6-bromo-N-methylpyrazine-2-carboxamide

Product 1

HCID 151481226-bromo-3-methyl-4(3H)-PteridinoneYield 89%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a mixture of triethyl orthoformate (70 mL) and acetic anhydride (70 mL) was added 3-amino-6-bromo-pyrazine-2-carboxylic acid methylamide (12.7 g, 55 mmol; see Example 16 (b) above) with stirring. The resulting solution was heated at reflux for 2 hours and allowed to cool to room temperature. The precipitate that formed was collected, washed with ethyl acetate, and dried to afford 6-bromo-3-methyl-3H-pteridin-4-one as a white solid (11.8 g, 89%). 1H NMR (300 MHz, DMSO-d6) δ3.54 (s, 3H), 8.70 (s, 1H), 9.15 (s, 1 H); 13C NMR (100 MHz, DMSO-d6) δ34.03, 133.28, 137.82, 152.39, 152.70, 153.33, 159.19.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 2 hours
  3. customThe precipitate that formed
  4. customwas collected
  5. washwashed with ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-6b374c727c9041d5bdc0f7ea941124ea
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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